omega-Dialkylaminoalkyl ethers of 5-endo-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-hydroxyimines with platelet antiaggregating, antiarrhythmic and local anesthetic activities.
The synthesis of 1,3,3-trhimethyl-5-endo-(1-piperidinyl)- and -5-endo-(4-morpholinyl)-2- oxabicyclo [2.2.2]octan-6-hydroxyimine 3 and 4 starting from 5-endo-bromo-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine+ ++ and excess piperidine or morpholine is described. Compounds 3 and 4 gave a series of omega-dialkylaminoalkyl ethers 5 by reaction as sodium salts with omega-chloroalkyldialkylamines in DMF solution. Some of aminoethers 5 showed in mice an appreciable antiarrhythmic and local anesthetic activity, as well as a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid.
Schenone
S
S
Istituto di Scienze Farmaceutiche dell'Università, Genova, Italy.
Ranise
A
A
Bruno
O
O
Bondavalli
F
F
Losasso
C
C
Donnoli
D
D
Cenicola
M L
ML
Marmo
E
E
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000758:Anesthesia; D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001794:Blood Pressure / Q000187:drug effects; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006339:Heart Rate / Q000187:drug effects; D006801:Humans; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D007274:Injections, Intraperitoneal; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D014693:Ventricular Fibrillation / Q000139:chemically induced / Q000517:prevention & control
D000588:Amines; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D001643:Bridged Bicyclo Compounds; D007097:Imines; D010975:Platelet Aggregation Inhibitors